


If You're Gonna Play the Game, Boy, You've Gotta Learn to Play it Right

by SupernaturalFlavoredLollipop



Category: Supernatural, Supernatural Novels - Various
Genre: Betting, Dean Winchester Smut, Embarrassment, F/M, Flirting, Fluff, Ghouls, Hunters, Nakedness, Nudity, SMUTTY SMUT, Sex, Smut, bet, not shy, sam is pissed, wager, who will blush first
Language: English
Status: Completed
Published: 2015-04-29
Updated: 2015-04-29
Packaged: 2018-03-26 07:56:01
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,562
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3842998
Author URL: https://archiveofourown.org/users/SupernaturalFlavoredLollipop/pseuds/SupernaturalFlavoredLollipop
Summary: <blockquote class="userstuff">
              <p>***Request***<br/>You and Dean have a bet going on, for $500, to see who can make the other one blush first. Things quickly get out of hand.</p>
            </blockquote>





	If You're Gonna Play the Game, Boy, You've Gotta Learn to Play it Right

“You two _what_?” Sam asked, eyes wide. “I swear to God, I leave you alone for three minutes, and this is what happens?”

 

“Well, I mean, if we're being honest, you left us alone a lot longer than three minutes...” Dean shot you a knowing look. “I'm no minute man, Sammy.”

 

Sam gave Dean the dirtiest look you had ever seen.

 

“Oh Jesus, Sam, you leave us alone all the time. You aren't our Dad for Christ's sakes. We're adults... and it was...”

 

“What? It was what?” Sam shook his head.

 

“Bound to happen eventually?” You supplied the answer helpfully.

 

“Yeah, why are you so worked up?” Dean raised an eyebrow at his younger brother.

 

“Why am I so worked up? _Why am I so worked up_?” Sam stood up abruptly. “Maybe because I've been working this _freaking case with you two morons for two months,_ and you've been playing this _stupid game for two months_ , and I leave to go get groceries and be the adult, _like I've been doing for the past two months_ , and I come back and you're both _fucking naked!_ ” He put up his hands in a sign of surrender. “I'm obviously the only one who's taking this ghoul infestation seriously. So by all means, keep playing grab-ass. I'll get my own room.” He grabbed his laptop and bag, and stalked out of the room.

 

Dean looked at you sheepishly. He was wrapped in a bedsheet; you were wrapped in a towel. It was pretty obvious what the two of you had been up to. “I thought he thought the 'Make Y/N Blush' game was funny.”

 

You rolled your eyes. “It was the 'TRY to Make Y/N Blush' game, and you were always way more into it than Sam was, Dean.”

* * *

_Two Months Ago_

 

“Y/N. Nice to see you again.” Sam smiled and waved as you approached their table at the coffee shop in downtown Memphis.

 

“Hey, Sam. Dean.” You nodded at the brothers. It had been a while since you'd seen them, but you all went back, _way back_. Your fathers had known each other. You'd all grown up on the road, hunting. Your fathers had both met untimely ends; you all knew you probably _all_ would as well. In fact, rumor had it the Winchesters already had, several times, but you hadn't asked. “This case must be serious. Can't handle it yourself? Had to call in the big guns?” You slid into the booth opposite them.

 

Dean sized you up. He had been doing that since, oh, forever. He'd kissed you, once, when you were seventeen, in the back of your dad's old Dodge Charger. But that was as far as it ever went. But his eyes, those green eyes... they always took it farther. He smirked at you. “The big guns? That's what you call yourself these days?”

 

“I don't have to call myself anything. My reputation precedes me.” You looked from one to the other. “Obviously. Or you wouldn't want my help. So what's going on?”

 

“It looks like a ghoul, but we aren't sure. People keep going missing, then reappearing the next day or so later, as though nothing happened.” Sam explained.

 

“You're local, and we... hear you're good with ghouls.” Dean stated bluntly. Good with ghouls was an understatement. A ghoul had killed your father. You'd made it your mission to kill as many as possible. You knew every way to kill them. You'd taken out over 300 in the past ten years. You were the ghoul master. The problem was finding them. And ghouls talked. If they knew you were in town, they'd cover their tracks.

 

“How many do we think there are?” You leaned forward.

 

“Two or three. Not many. A family disappeared a month ago... and stayed gone. Trail went cold. But we think they're still in the area.” Sam was on his laptop. Some things never changed.

 

“So what do you say? You want to gank a few more ghouls and hang out with the two coolest guys you know?” Dean winked at you.

 

“Always.” You gave him a half smile.

* * *

 

“I know you guys stay in dives, but this place is a total shit hole.” You sized up the crappy motel the Winchesters were currently living in. “And it has no more rooms.”

 

“We can get you a room at the place down the street.” Sam suggested. “It's only fair we spot you. I mean, we did call you in on this.”

 

You shook your head. “It's fine. I can crash on your pull out couch, if that's all right with you.”

 

Dean nodded. “Whatever floats your boat, Sweetheart. But fair warning- I sleep naked.”

 

Sam rolled his eyes. “He doesn't.”

 

You shrugged. “Sleep as naked as you want. I'm not shy.”

 

Dean's ears seemed to pick up on that, and his mood instantly brightened. “Oh, that sounds like a challenge. Does that sound like a challenge to you, Sammy?”

 

Sam rolled his eyes. “If we were fourteen it might, Dean, but last time I checked, we're _in our thirties_.”

 

Dean rubbed his hands together deviously. “Sounds like a challenge to me.”

 

You raised your eyebrows. “A challenge? What kind of challenge. You already know I'm not shy.”

 

“I'll bet you...” Dean thought about this for a second. He pulled out his wallet and looked in it, cringed, and put it away. “I'll bet you _five hundred dollars,_ that I can make you blush, before this case is over.”

 

You looked at him coolly. “I'm calling bullshit that you even have five hundred dollars in that wallet... but sure, I'll take you up on that bet. But same goes for you. If I make you blush, I get five hundred dollars.”

 

Dean shrugged. “Deal.” You both shook on it. “I don't blush, Princess.”

 

“Neither do I, Princess.” You replied. “And in case you forgot, I've seen both of you naked before. Twice.”

 

“Twice?” Sam asked, looking a bit uncomfortable. You nodded. “I knew about the skinny dipping incident, but when was the second time?” he asked, gulping.

 

You winked at him. “The world may never know.”

* * *

 

Dean tried hard to make you blush, he really did. When it became apparent that calling the fold out couch the “pull out method” wasn't phasing you, and calling his bed the “baby maker” and the “scream machine” wasn't working either, he got more inventive. His showers ended with him spending hours dressed only in a towel. One bath time ended with him dancing around in said towel singing an impromptu version of George Michael's “I Want Your Sex”, complete with pelvic thrusts and gyrations. This only ended up causing both you and Sam to nearly die from laughing so hard, and Dean to pull a muscle in his groin.

 

Sam finally got fed up with the whole game, the more inappropriate it all became. To be honest, you and Dean were just bored. You were _all_ bored. Days became weeks, weeks became a month, and as it got on to two months, the ghouls seemed to have given you the slip. You had to admit, both you and Dean were acting like juveniles, because there was literally nothing to do, and a desperate amount of sexual attraction was building between the two of you. When he wasn't acting like a dumbass, he was hot. This was the way it always worked, every time you were together; you were just never together long enough for it to go anywhere.

 

You couldn't seem to get him to blush, either. You'd try your hardest. You'd lean over his shoulder, lips just skimming his earlobe, as you whispered dirty things to him first thing in the morning, then smile innocently at him, grab some coffee, and walk away. But the man was made of tougher stuff than you gave him credit for. He didn't break.

* * *

Thirty Minutes Ago

 

You were in the shower, just finishing washing off the soap and rinsing conditioner from your hair, when you heard the door open. You rolled your eyes. Sam had left to go buy groceries, so you knew it was Dean.

 

“Dean, what are you doing?” You called out through gritted teeth. What did it take to get some alone time around here?

 

“Brushing my teeth. I'm turning in early tonight.” Came the reply. You heard the water turn on in the sink, and then your towel was pulled from it's resting place over the shower rod.

 

“Hey, I'm gonna need that towel, Dean!”

 

“What for?”

 

“Uh, I don't know, _maybe to dry off with?_ ” You pursed your lips, waiting for him to return the towel so you could turn off the shower.

 

“You have another one.”

 

You rolled your eyes. You seemed to do that a lot with him around. “I'm a girl. We use two towels.”

 

You heard some tooth brushing going on, some gargling, and the sink go on again. “Well, princess, I'm using this one. So either dry your hair and body with the same one, or whatever, leave your hair wet, leave your body wet, go naked, I don't know. Figure it out.” He replied flippantly.

 

You sighed. And then you got a horrible, wonderful idea. It was the Hail Mary of all ideas, and it was going to get you that five hundred dollars. You turned off the water, and pulled your lone towel from the shower rod. You dried off carefully, and then wrapped the towel around your hair. You heard Dean leave the bathroom, carelessly throwing his used towel on the towel rack.

 

You stepped out of the tub, onto the bathmat. You hesitated a minute, but the thought of Dean being shocked as all get out, and five hundred dollars cold hard cash in your hand, and the glory of winning the bet, urged you to proceed. You yanked the bathroom door open, and waltzed out into the motel room. Dean was lounged on his bed. He glanced up as you entered the room, not really paying attention, but as soon as he saw what you _weren't_ wearing, his eyes grew huge. And then you saw it. The pale pink flush creeping across his cheeks, turning to deep crimson. _Success._

 

He'd commented that you'd only needed one towel. So you'd only used one. It was on your head. Other than that, you were completely naked. And Dean was blushing like crazy.

 

You stood there, gloating, hands on hips. “You, sir, owe me five hundred dollars.” You said, smiling.

 

“Holy shit.” Was all he could say.

 

“That's all you have to say?”

 

“Um... okay. Either put some clothes on or... I don't know. I'm thinking some really, really X-rated things right now.” Dean licked his lips.

 

“How x-rated?” You asked. Your interest was piqued.

 

“Like Casa Erotica X-Rated. Only without Gabriel outtakes.”

 

“Gabriel outtakes?” What the hell was he talking about. Who was Gabriel?

 

“Never mind.” Dean shook his head. “Seriously, Y/N. Please, for the love of God, either put some clothes on or come over here and climb into-”

 

“If you call your bed the 'scream machine,' it's NOT going to happen.” You warned him.

 

“If it happens, I swear I'll never call it the 'scream machine' again.” Dean was looking at you with eyes so intense, it was making you hot. You nodded, approached the side of his bed, and, removing the towel from your hair, slid under the sheets.

 

“How long til Sam gets back?” You asked.

 

“Long enough.” Dan replied, pulling you over to him, and pressing his lips to yours, parting yours slightly and sliding his tongue into your mouth. You ran your hands up his chest, under his shirt.

 

“How about we lose this?” You suggested. His shirt came off. “And... the rest of it?” He was happy to oblige. Now you were both naked. You rolled over and he was on top of you, and you were all arms and hands, exploring one another's bodies, grasping each others hair, groaning and kissing and whispering swear words into each others ears when things felt _just right_. At some point it was decided that you were going to go all the way and a condom was procured; you'd been eyeing each other for years, and the time was right, _the time was now._

 

You were in the full throes of passion when the bedroom door opened, without either of you noticing. You had Dean under you, one hand on his chest, your head thrown back, yelling his name, when the light flipped on. Both yours and Dean's heads immediately snapped towards the door. “Shit!” You both swore in unison, grabbing for the closest thing you could find to cover with. Sam was back, and Sam was not happy to find you both _en flagrante._

 

* * *

 

Dean found Sam outside in the Impala. He'd thrown his bag and his laptop in the front seat, and was laying in the back, trying to sleep. Dean climbed in behind the wheel. He'd left you in the motel; he'd wanted to pick right back up where you'd left off. You'd told him there was plenty of time for sex later, and to go fix things with Sam.

 

“Hey, Sammy.” Dean said, shutting the car door.

 

“Go away, Dean. You reek of sex.”

 

Dean sighed. “Listen, sorry, dude. I should have... put a note on the door or something.”

 

“You... you totally don't get it, do you?”

 

“Get what?”

 

“It's not about a fucking note.”

 

“What?”

 

“I don't care about walking in on you.”

 

“You don't?”

 

Sam sat up and gave Dean a look that said _really bro?_ “Dean, I've walked in on you with girls plenty of times. It's not exactly surprising anymore.”

 

“So what's the problem? You got a thing for Y/N?”

 

Sam sighed. “Oh my God. No.”

 

“Then what is it?” Dean gave him an exasperated look. “Throw me a bone here. I don't know why you're so pissed.”

 

“Seriously?” Sam ran a hand through his hair. “Because I'm the only one taking this seriously. You and Y/N have been making eyes at each other for the last few weeks, and I've had to sit here and watch it like a bad porno, while trying to locate some ghouls that are evading us like we're a bunch of jackasses. It was funny at first, you guy's game, then it got old. Fast. Then I come home to you two naked... it's just... _seriously_. Do some real work. Have sex one we gank the ghouls.”

 

Dean nodded. “Fair enough. I get it. We've been acting like idiots.” He paused. “Do I always act like an idiot when she's around?”

 

Sam gave Dean a flat look. “Pretty much, yeah. Since you were twelve.”

 

“I had a sneaking suspicion.” Dean opened the car door. “You can come back in the motel room. I swear we'll behave until the hunt is over.”

 

Sam shook his head. “Nah. Get it out of your system. I'll sleep in here tonight.”

 

“In my defense, she came out of the bathroom in _absolutely nothing_. I was a weak man, Sam.”

 

Sam chuckled. “Dean, please tell me one thing.”

 

“What's that?”

 

“You didn't lose five hundred bucks to her did you?”

 

“About that, Sam... could I borrow four hundred? A deal is a deal...”

 

 

_Carry on my Wayward Son..._


End file.
